New azo dyestuffs



UNITE STATES PATENT OFFICE -H.ARBY GRIMMEL, F W'IESDORF, AND HEINRICH CLINGESTEIN, OF COLOGNE-ON-THE- RHINE, GERMANY, ASSIGNORS '10 GENERAL ANILINE WORKS, INC., OF NEW YORK,

N. Y A CORPORATION OF DELAWARE NEW AZO DYEST'UEFS Ito Drawing. Application filed July 28, 1927, Serial No. 209,171, and in- Germany August 19, 1926.

The present invention relates to the new unsulfonated and uncarboxylated azo dyestufis of the general formula:

wherein R represents the radicle of an unsulfonated and uncarboxylated coupling component, such as, for instance, an unsulfonated and uncarboxylated naphthoharylide of the 2.3-hydroxynaphthoic acid, hydroxynaphthocarbazole, diaceto-acetic acid arylide and the like, and wherein n is 1 or 2.

The new dyestuffs may be'produced either in substance or on a substratum or on-the fiber by coupling a diazotized amino fluorenone with one of the abovementioned components forming insoluble azo dyestuif. The dyestuifs produced are yellow to black powders insoluble in water-and fast to light and to washing. According to the selection of the coupling components yellow, red, violet and black dyestufis can-be produced which show outstanding fastness on the fibre.

The following examples serve to illustrate our invention, which can be varied according to individual requirements Ewample -1.-Well boiled and dried cotton am is impregnated with a solution containmg per litre 12 grams of 2.3-hydroxy-naphthoic acid anilide, 20 cc. of caustic soda solution of 34 B., 25 cc. of Turkey red oil, wrung out and developed without drying witha diazo-solution previously freed from mineral 40 acid by the addition of acetate, containing 5 grams of mono-amino-fluorenone perlitre. After the formation of the dyestufl the yarn is rinsed and soaped, the dyestulf thus produced is a reddish powder insoluble in water yielding a very beautiful red shade on cotfluorenone and ,B-na'phthol a beautiful red 90 ton, fast to light and to washing. The dye stufl probably has the formula:

Ec'ample 2.By the use-of mono-amino has the same qualities as described in xamp1ei1.- The dyestuff probably has the formu a:

Example 3. By the use of mono amino- HO n v Example .4.-By the use of 2 :7 -diamino fluorenone and 2.3-hydroXy-naphthoic acid-aniformula:

Example 5.By the use of 2.7-diamino-fluorenone and 7-hydroxy-naphtho-carbazole a ample fl. The dyestuff probably has the formula v Example 6.Fibres impregnated with diaceto-acetic-acid tolidide and developed with the tetrazo compound of diamino-fiuorenone are dyed a powerful bronze-yellow with the same qualities as mentioned above. The dyestuff probably has the formula:

cm on;

- omooimoomo-O-nmooimooom "on. om

r omoobnbemrOOumoodmodom dyestulf probably has the formula: lide a violet dyestuff is obtained showing the same qualities as mentioned in the preceding examples. The dyestufi' probably has the v deep black dyestufl' is obtained in a similar manner. Its qualities are the same as in Ex-' l droxy-naphthoic acid anilide. The dyestuif separated from this solution is filtered off,

washed with water and dried. It is a reddish powder insoluble in water yielding a red pigment fast to light and to washing. The

The process can be carried out in a similar manner with other amino-fluorenones and other arylides of 2 3-hydroxy-naphthoic acid or similar hydroXy-naphtho-carbazoles as Well as with other diaceto-acetic acid arylides and derivatives thereof.

We claim i 1 I lQProcess for the manufacture of an azo dyestufi' insoluble in water, by coupling a diazo compound of an unsulfonated and uncarboxylated amino-fiuorenone with an unsulfonated and uncarboxylated coupling component. 1

g 2. Process for the manufacture of an azo dyestuff insoluble in water by coupling the diazo compound oftheunsulfonated monoamino-fluorenone with 2.3-hydroxy-naph- 0 thoic acid anilide. a 1

3. As new products the unsulfonated and uncarboxylated azo dyestufl's of the general formula:

wherein R represents the radiele of a coupling component.

4. As new products the unsulfonated and uncarboxylated azo dyestuffs of the general formula:

wherein R represents the radicle of a cougling component and X represents either hyrogen or the group: i

5. As a new product the unsulfonated and uncarboxylated azo dyestuif of the formula:

being in a dry state a reddish powder insoluble in water and yielding on cotton a beautiful red shade fast to light and washing.

-. 6. As new productsthe unsulfonated and unearboxylated azo dyestuffs of the general formula:

.tyl-HN-OO wherein X represents hydrogen or the group- 40 mg:

aryl-HN-OO 5 In testimony whereof we have hereunto set our hands.

HARRY GRIMMEL.

o HEINRICH CLINGESTEIN. 5 

